


Triple Date Night

by Bi_Dean67



Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Dean Winchester, Drunk Dean Winchester, Established Castiel/Dean Winchester, Gay Bar, Jealous Castiel (Supernatural), M/M, Protective Castiel (Supernatural), Shower Sex, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-11-12
Updated: 2020-11-12
Packaged: 2021-03-09 19:53:43
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,526
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27521842
Author URL: https://archiveofourown.org/users/Bi_Dean67/pseuds/Bi_Dean67
Summary: Dean and Cas have a monthly double date night with Jesse and Cesar at Apollo's Tavern, the only gay bar in 15-mile radius. This time Sam and Eileen want to come with.
Relationships: Castiel/Dean Winchester, Cesar Cuevas/Jesse Cuevas, Eileen Leahy/Sam Winchester
Comments: 2
Kudos: 62





	Triple Date Night

**Author's Note:**

> Thanks for clicking on my work! This is my first fic and I hope you like it! There is a sex scene that doesn't really serve the plot so if you don't like it skip it. I took some liberties with the time line and other plot related things so remember this is fiction and I know that's not when/what happened.

Eileen is in Lebanon visiting Sam for the week and it happens to be the week Dean and Cas are supposed to have their monthly double date night at Apollo's Tavern with Jesse and Cesar. Jesse and Cesar are retired so it's up to Dean and Cas to decide when they meet up. They had a busy month with multiple hunts and one taking an especially long time, so this was there last chance to have this month’s date night. Usually it wouldn't be problem if they went out why Eileen is in town, but this time she and Sam want to join them. Dean is usually happy to spend time with Sam and Eileen, but date night at the only gay bare in 15-mile radius isn't exactly how want to spend time with his little brother and said little brother's girlfriend. Date night is for playing dumb drinking game and talking about their relationships, and when they get drunk enough sex. Sammy does not need to know that he calls Cas "sir" when they fuck! Sam has been trying to convince Dean to let them come for five minutes while Dean cleans the kitchen and doesn't help by the way. 

"I don't understand, we've gone out with you guys plenty. Why is this any different?"

"I already told you Sammy, we are going to GAY bar."

"Straight couples are allowed in gay bars Dean!"

Of course, Dean knows that, but he needs a reason to tell Sam he can't come.

"We're just going to get drunk and hang around. Do you really want to spend your limited time with Eileen with a bunch a drunk dudes? And if you're gonna keep bothering me you could at least fucking help clean" Dean say with an eye roll.

"Come on Dean, you’re not 'a bunch of dudes' you're my brother and his friends. why don't want you want me there?"

Dean puts down the sponge he was using to scrub the sink. He feels bad now, it’s not that he doesn't enjoy time with Sammy it’s just, he can’t let loose like he does with Sam there. Dean sighs, it is just a onetime thing, so finally he concedes and tells Sam he can come. 

"Alright Sam, you guys can come, but don't say I didn't warn you when Jesse want to play truth or drink."

"Yes! I'll go tell Eileen."

"Whatever, we leave at 7"

Dean abandons his cleaning to find Cas. He finds him in their room reading some article about a bee migration.

"Dean! Did you know bees migrate south for the winter just like birds? But only tropical bees, the migration strategy can be fatal to temperate bees."

"That all sounds real interesting Cas, but I came to tell you Sam and Eileen are coming to Apollo's Tavern with us," Dean tell Cas, not sounding happy about it.

"You sound thrilled," Cas is finally understanding sarcasm, and is getting a little too good at it in Dean's opinion. 

"Yeah, but we all always talk about, you know... gay shit. I don't really want my little brother around to hear Cesar ask who bottoms most, like he always does even though every time I choose to drink instead of answer!" Dean says getting a little off track at the end. 

"I'm sure Jesse and Cesar won't ask stuff like that while Sam is there."

"Yeah until they're drunk enough" Dean pouts.

Cas stands up and walks over too Dean, pulling him in by the hips for a sensual kiss. Dean responds by raping his arms around Cas's neck opening his mouth just enough to add a little tongue. Cas pulls away a little, still holding onto Dean.

"You worry too much. Come take a shower with me, I promise the last thing you'll be thinking about is you brother" Cas says with an exaggerated wink that makes Dean huff a laugh.

They each grab a towel and head for the shower. They strip quickly, usually they would add a little finesse, Dean would make a show of undoing his pants and slowly dragging them down, or Cas would undress Dean, kissing his skin as he removed each piece of clothing. Right now, they actually did need to shower and get ready, so clothes came off in hurry and Cas dragged Dean under the stream of hot water. Cas kissed Dean roughly, quickly moving on to attack his neck, Dean was definitely going to have a hickey or three, but he wasn't thinking about that now. Cas angel mojod some lube onto his fingers and began circling Deans hole. He sunk his finger in while nibbling on Dean’s ear. Deans sighed with pleasure and Cas almost immediately added another finger. After about five minute, two fingers, and whole lot of begging later Cas finally pulled his fingers out and lifted Dean, Dean wrapped his legs around Cas's waist. Cas slammed Dean back against the shower wall and sat him down on his cock. 

"Fuck" Dean shouted as he was stretched open. Cas gave him a moment to get use to his impressive size.

"Ready baby?"

"Hell yeah, Fuck me!" Cas began slamming his hips up and into Dean, neither of them expecting this to last long.

"So good for me, Dean. You take my cock so well. I love you so fucking much" and Chuck did Dean love it when Cas talked like that in his deep fucked out voice.

"So big Cas! So close! PLEASE! please please please" after that Dean just started babbling nonsense. Lucky for Dean, Cas was getting close too.

"Whenever you're ready baby, you can come."

After a few more thrusts Dean came, practically screaming, Cas followed close behind. 

For a moment they stood there, Cas's softening length still in Deans ass, Dean resting his forehead on Cas's, a sated smile on both their faces. Cas gave Dean a gentile kiss and set him on his feet. 

"Fuck that was..." Cas trailed off.

"Yeah" Dean agreed knowing exactly what he wasn't saying, " now wash my hair you fucked all the energy out of me."

"Oh of course I imagine me holding you up and doing all the work was very tiring for you." Yeah Cas is definitely getting too good a sarcasm. 

"Just a testament to how good you are" Dean smirked at Cas, "plus you have all that angel stamina, it's not fair."

"alright alright, I will wash your hair. On your knees, so I can reach your hair better."

"Yeah that's why" Dean mumbled.

"What was that?"

"Nothing Sir." Cas shook his head fondly and began washing Dean's hair.

They finished the rest of the shower quickly and got dressed. Dean wore jeans, a black Metallica t-shirt, a red flannel and his leather jacket. Cas dressed similarly in jeans and a plain black long sleeve henley and of course his trench coat. Dean always insisted he dress casual for date night but he could never argue him out of the trench, he earned himself a spanking for it once but that was more because of disrespect and some choice words he had used. It was almost seven so Dean and Cas headed to the War Room to wait for Sam and Eileen. They didn't have to wait long; Sam and Eileen came in a minute later ready to leave. They all packed into the impala, Cas sitting shotgun with Sam and Eileen in the back, Dean of course was driving even though Cas always had to drive back when he inevitably gets sloshed. 

Dean has already texted Jesse to let him know Sam and Eileen would be joining them. Jesse said it was cool with them, but Dean was still a little on the fence about Sam being there, but it was too late now anyway.

"I've never been to a gay bar, I'm excited" Eileen said and signed. 

"Apollo's is chill, it's like any other bar but with more flags and the bartender is an actual mixologist which is awesome... not that I get like fruit drinks or anything I just mean it’s like cool or whatever" Dean responded flustered by his own words while Sam translated with an eyeroll and chuckle. Dean hadn't even thought about the actual drinks, he wasn't getting apple-tinis or anything like that, but their usual bartender made a really good mint lime mojito. Whatever, he could just get a whisky and a couple beers tonight, sometimes he got that surly no one would say anything. 

The rest of the ride was short and spent telling Eileen a little bit about Jesse and Cesar. 

They were the first to arrive. They usually sat at the high tops by the bar, but since they had the extra two people they sat at the round booth in the corner of the bar. The bar was pretty busy, but that was expected for a Friday night. 

"This place is packed; it's going to take forever to get drink" Sam complained.

"Nah, Donnie's bartending tonight. I can get us some drinks. I'll go ahead and just get Jesse and Cesar their regulars. What do you guys want?"

"Dean why don't you let me go, I don't mind."

"Come on Cas, now's not the time to get all jealous. Besides, I think he has a boyfriend now."

"That's never stopped you two from flirting before" Cas says kind of pissed.

"I would hardly call it flirting, he just hits on me and we get faster drink and sometimes even free shots."

"Wait wait wait, Dean you flirt with the bartender?!" Sam says shocked.

"Again, not really flirting and only for drinks. Why are you so surprised?" Why was he surprised? He had seen Dean flirt with bartenders before, but they were all women. When he thought about it, outside of him being with Cas, Sam had never seen Dean as gay. Not that he cared it just kind of through him off.

Sam never really answered Dean's question, but lucky for him Cas spoke up.

"Well I'll go with you; you can't carry all the drinks anyway"

"That's what trays are for Cas" Dean said in a bratty tone that had Cas raising one eyebrow. Dean looked a little sheepish after that, not liking being scolded in front of Sam, even with just a look.

"I'll go with you Dean, I don't know what I want anyway" Sam offered, mostly because he was curious about Dean and Donnie's flirting.

"Perfect lets go!"

Donnie was finishing up with another customer when Dean and Sam pushed through people to the bar. 

"Donnie!" Dean shouted to get his attention. Donnie saw Dean and immediately by passed all the other customers for him. Sam was a little shocked they got service so quick, even though Dean said they would. 

"Dean! Feel like I haven't seen you in a while. Who's your friend?" he asked with a little more than curiosity in his tone. 

"This is my brother Sammy. My very straight brother here with his girlfriend" Dean overly clarified.

Donnie frowned playful. "Don't you have a boyfriend anyway" Dean asked him.

"Yeah but we have an open relationship" he winked.

"That explains a lot, but I am still in a very monogamous relationship."

"Well if that ever changes you know where to find me. What can I get for you guys? Mojito for you Dean?"

"Mojito!?" exclaimed Sam laughing. 

"Shut up bitch! I’ll have a whiskey and the usual for the rest of plus whatever he and his girlfriend want" 

"Get mojito if you want Dean, it is a gay bar after all" Sam joked.

"What's that supposed to mean" Donnie and Dean said at the same time. Sam immediately looked flustered and tried to back track.

"I was just kidding. I I I didn't mean anything by it. I just uh..." Dean and Donnie started laughing, Sam was so confused.

"We're just fucking with you Sam."

"Oh haha. I knew that" Sam said awkwardly.

"Uh just two Sweetwater 420s for me and Eileen" Sam ordered after a moment of kind of awkward quietness, well awkward for him, Dean seemed quite amused. Donnie handed them a tray with the two beers, a glass of whisky, an old fashioned, and a jack and coke on it along with an entire bottle of raspberry Smirnoff. 

"Thanks man" Dean said taking the tray, leaving Sam to get the Vodka.

"what the hell is this for" Sam asked, referring to the vodka.

"Oh, that's for Cas. He likes to get a little buzzed while we're here."

"Oh yeah angel metabolism."

When they get back to the booth Jesse and Cesar are there. Dean sets the drinks down and says hello.

"No mojito Dean? You look forward to those all month" Cesar points out. 

"No, I don't. I got it like once. I like whisky" Dean responds blushing. Cesar doesn't press on it, seeing it made Dean uncomfortable. Sam tried not laugh after the obviously lie but failed miserably and earned a glare from Dean. And Cas? He wasn't expecting that, Dean sure, but what does Cas care if he teases Dean?

"Sam, aren't you going to introduce Eileen" Cas prompts to change the subject not liking the way Sam was laughing at Dean for liking what he considers a woman's drink. Cas is really the only one who knows how long it took Dean to start letting himself enjoy things like "girly" cocktails. The monthly nights at Apollo's Tavern with Jesse and Cesar have really helped Dean embrace the part of himself he considers "gay", and Cas will not let Sam ruin any of his progress. 

"Yes of course! Jesse, Cesar this is my girlfriend Eileen"

"Hello Eileen, it's nice to meet you" Cesar say and signs, much to Eileen's surprise and delight. Eileen is great at reading lips, but with the way they are sitting it is hard to see everyone when they speak so having people who can sign really helps. 

Jesse greets Eileen as well while Cesar interprets for him. Everyone is having a great time catching up. The boys told Jesse and Cesar about the hunts they had been on recently and Cesar and Jesse told them about their trip back to Mexico. Eileen told a story about a witch she had hunted a few weeks back, and by then everyone was ready for another round. Cas offered him and Sam to get the drinks. Donnie wasn't as quick to serve Cas, so he took the moment to talk to Sam.

"I am going to order Dean his favorite mint lime mojito, that he does in fact look forward to all month, and you are not going to say fucking word about. I know your teasing is in good fun, but it takes a lot for Dean to do things you may consider 'gay'" Cas says using air quotes. 

"Jeez Cas I won’t, but Dean knows I'm joking. Besides since when does Dean care what I think?"

"For such a smart man, you sure are fucking dense Sam. When you’re around Dean feels the judgment he felt from John, not to the same extent but it's there and he feels the need to be the manly man older brother you know him as. It's not your fault Sam, but it doesn't help when laugh and validate his insecurities."

"Shit Cas, I'm sorry. I really didn't think about it like that."

"I know, just try to be more aware"

Before Sam can respond Donnie is ready for to take their order. Cas gets Dean his Mojito and another round of the same for everyone else. He also gets three orders of nachos because they're Dean's favorite and he's pretty sure no one has eaten. 

Back at the table Cas hands Dean his mojito and Dean looks at Sam who is purposefully not paying attention. Dean leans into Cas and kisses him on the cheek as a silent thank you. 

After the nachos had been devoured and they were on to round three of drink, the inevitable happened. 

"Let's play truth or drink!" Jesse suggested. Dean groaned internally. They always played truth or drink and its usually really fun, they ask embarrassing and often sexual questions, but it just stayed between them. With Sam there it's going to be so awkward. 

"No, we always play that, let’s do something else" Dean suggests. No one agrees with him though, everyone want to play, except for Cas who seems indifferent because he seems to be incapable of being embarrassed. Dean reluctantly agrees to play. 

"I'll go first" Jesse offers.

"Hmmm, Cas, have you ever had sex with a woman?"

"Yes, well... kind of. She was reaper does that count?" Everyone seems to agree that it does count. Dean looks annoyed by the question and can't help how it makes him feel jealous.

"Eileen, what is the biggest age gap you've had with a partner?" Cas asks. He's pretty bad at thinking of questions and it took him a while to get the game, so he usually asks questions he's heard before, including this one.

"seven years. Dean, where is the grossest place you have had sex?" Dean looks to Cas. It's honestly hard to choose. When they finally got together, they would fuck pretty much anywhere they felt the urge. Dean ends up finishing his drink instead of answering. Eileen laughs and asks, "that bad?" Dean and Cas nod their heads, and everyone laughs.

"Ok Cesar, have you and Jesse ever messed up a hunt because you got distracted having sex?"

"Definitely, haven't you?"

"Hey, now it's not my turn" Dean says, not answering the question even though that just makes it obvious the answer is yes.

"Alright Sam, what was your longest dry spell?" Sam takes a drink knowing the answer is embarrassingly long. It took a couple years for him to get back out there after Jess.

"Cas, who is your hall pass?" 

After some explaining from Dean, Cas finally answers with, "I don't have one, I would never fornicate with someone that isn't Dean." 

Everyone boos, but Dean swoons and is just tipsy enough to give Cas a pretty PG-13 kiss.

The night goes on like that for another hour or so and everyone, except Cas, is drunk. The questions vary in appropriateness, which has a direct correlation to drunkeness.  
Jesse asks Dean who bottoms more and Dean know if he drinks he'll be given away anyway so he finally admits he bottoms more, but Cas unnecessarily adds that Dean bottoms almost exclusively, which earns him a slap on the shoulder and blush from Dean and Sam. Dean makes a new rule, no questions about kink while siblings are present, after Eileen asks him what his biggest kink is. He still had to drink for the question but if it went on like that Dean would end up shit faced. 

Eventually Cesar asks Cas when he's going to propose to Dean. Cas does not know what to say, he and Dean had never talked about getting married. Cas was an Angel after all but calling Dean his husband was intriguing.

"Do you want to get married" Cas asked Dean.

"Well, I, I mean, maybe. Your definitely it for me but you’re not even human, how would we get a marriage license." Dean was not prepared for this conversation. He had secretly thought about marring Cas, but it just didn't seem possible for them, always dealing with some world ending crisis. Would they have a wedding? Who would officiate it? How would they get marriage license? Dean was not sober enough for these thoughts.

"But do you want to?"

"... yes"

"Ok. Dean will y-" 

"Oh, hell no" Dean interrupts Cas, "I am not getting proposed too in a bar, drunk, in the middle of a game of truth or drink. Do it another time with more pizazz and a ring." 

Everyone laughs including Cas who agrees to plan it out and propose at a later date. They decide that was a pretty good way to end the night. Everyone says their goodbyes and head out. 

Dean is giddy on the car ride home. Cas is going to propose to him! He gets a little overly affectionate in the car and Sam clears his throat obnoxiously, so he just sits really close to Cas with his face in Cas's neck. Dean has big plans for when they back to the Bunker. He spends half the car ride planning out the rest of the night; for round one he would ride Cas hard, then round two would be gentle missionary, and then... Dean is waking up as Cas carries him through the garage? He must have fallen asleep in the car. Oh well, Dean will just surprise Cas with a wake-up blow job in the morning, he thinks as he falls back sleep in Cas's arms, trusting Cas will put him in pajamas and to bed as he had before. 

"Luh you" Dean mumbles just before passing out.

"Love you Dean" Cas says with a kiss to Dean's head even though he's already conked out.

**Author's Note:**

> Thanks for reading! Let me know what you thought!💜


End file.
